I think Bossk would win even though it's about an even macth. The Gorn nearly killed Kirk!, without laser guns and explosives...imagine if they were both equipped with weapons
Bossk has killed thousands of Wookies, and knowing how Wookies can easily rip off someone's limbs, Boosk should overpower the Gorn. Killing Wookies is more impressive than overpowering Kirk, who is only a peak-human.
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